US10793646B2 - Adhesive compositions comprising type-II cellulose - Google Patents

Adhesive compositions comprising type-II cellulose Download PDF

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Publication number: US10793646B2
Authority: US; United States
Prior art keywords: cellulose; lignin; adhesive; shr; residue
Prior art date: 2014-09-26
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Active, expires 2036-11-22

Application number

US15/511,195

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English (en)

Other versions

US20170275384A1 (en

Inventor

Ewellyn A. Capanema

Mikhail Y. BALAKSHIN

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Renmatix Inc

Original Assignee

Renmatix Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2014-09-26

Filing date

2015-09-25

Publication date

2020-10-06

2015-09-25 Application filed by Renmatix Inc filed Critical Renmatix Inc

2015-09-25 Priority to US15/511,195 priority Critical patent/US10793646B2/en

2017-08-15 Assigned to RENMATIX, INC. reassignment RENMATIX, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BALAKSHIN, MIKHAIL Y, CAPANEMA, EWELLYN A

2017-09-28 Publication of US20170275384A1 publication Critical patent/US20170275384A1/en

2020-10-06 Application granted granted Critical

2020-10-06 Publication of US10793646B2 publication Critical patent/US10793646B2/en

Status Active legal-status Critical Current

2036-11-22 Adjusted expiration legal-status Critical

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Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C08B15/08—Fractionation of cellulose, e.g. separation of cellulose crystallites
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G1/00—Lignin; Lignin derivatives
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B11/00—Preparation of cellulose ethers
- C08B11/16—Aryl or aralkyl ethers
- C08B11/18—Aryl or aralkyl ethers with substituted hydrocarbon radicals
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C08B15/02—Oxycellulose; Hydrocellulose; Cellulosehydrate, e.g. microcrystalline cellulose
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C08B15/05—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur
- C08B15/06—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur containing nitrogen, e.g. carbamates
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0057—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Xylans, i.e. xylosaccharide, e.g. arabinoxylan, arabinofuronan, pentosans; (beta-1,3)(beta-1,4)-D-Xylans, e.g. rhodymenans; Hemicellulose; Derivatives thereof
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic acids
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
- C08L1/02—Cellulose; Modified cellulose
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
- C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
- C08L61/14—Modified phenol-aldehyde condensates
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L97/00—Compositions of lignin-containing materials
- C08L97/005—Lignin
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L97/00—Compositions of lignin-containing materials
- C08L97/02—Lignocellulosic material, e.g. wood, straw or bagasse
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J101/00—Adhesives based on cellulose, modified cellulose, or cellulose derivatives
- C09J101/02—Cellulose; Modified cellulose
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J161/00—Adhesives based on condensation polymers of aldehydes or ketones; Adhesives based on derivatives of such polymers
- C09J161/04—Condensation polymers of aldehydes or ketones with phenols only
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J161/00—Adhesives based on condensation polymers of aldehydes or ketones; Adhesives based on derivatives of such polymers
- C09J161/04—Condensation polymers of aldehydes or ketones with phenols only
- C09J161/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J197/00—Adhesives based on lignin-containing materials
- C09J197/005—Lignin
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J201/00—Adhesives based on unspecified macromolecular compounds
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N23/00—Investigating or analysing materials by the use of wave or particle radiation, e.g. X-rays or neutrons, not covered by groups G01N3/00 – G01N17/00, G01N21/00 or G01N22/00
- G01N23/20—Investigating or analysing materials by the use of wave or particle radiation, e.g. X-rays or neutrons, not covered by groups G01N3/00 – G01N17/00, G01N21/00 or G01N22/00 by using diffraction of the radiation by the materials, e.g. for investigating crystal structure; by using scattering of the radiation by the materials, e.g. for investigating non-crystalline materials; by using reflection of the radiation by the materials

Definitions

FIG. 7 compares the performance of plywood PF wood adhesives containing SHR-50, and SHR-50 ⁇ AR (each containing type-II cellulose and lignin) in accordance with some embodiments of the invention, with otherwise identical plywood PF wood adhesives containing lignins that have been purified from SHR-50 (i.e., SHL-50) (see Example 4).
the ratio of type-I cellulose to type-II cellulose in the cellulose product, on a dry weight basis is about 0.5:9.5, 1:9, 1.5:9.5, 2:8, 2.5:7.5, 3:7, 3.5:6.5, 4:6, 4.5:5.5, 5:5, 5.5:4.5, 6:4, 6.5:3.5, 7:3, 7.5:2.5, 8:2, 8.5:1.5, 9:1, or 9.5:0.5.
the cellulose in the adhesive admixture or wood adhesive is at least 99 wt. % type-II cellulose on a dry basis.
Clause 8 The admixture of clause 7, wherein the residue has a moisture content of less than about 15 wt. % prior to the mixing.
Clause 43 The plywood of clause 42, wherein the plywood exhibits a bond strength of at least 90% of the bond strength of a different plywood prepared with an otherwise identical wood adhesive that does not contain the type-II cellulose.
SHL-50+AR was prepared by simply blending SHL-50 and SHR-50 ⁇ AR residues in the same proportions (by weight of solids) as obtained from the original SHR.
the PF replacement level was 30%, and the order of mixing was: (i) PF resin (ii) lignin/cellulose residue, (iii) 10 wt. % NaOH based on dry lignini/cellulose residue (added as a 25% by weight NaOH solution).
a control PF resin was also tested (“PF”), which does not contain any lignin or cellulose.
the performance of these adhesives was measured using the ABES system, similar to that described in Examples 1 and 3. The results are depicted in FIG. 7 .

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Analytical Chemistry (AREA)
Crystallography & Structural Chemistry (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Adhesives Or Adhesive Processes (AREA)
Dry Formation Of Fiberboard And The Like (AREA)
Compositions Of Macromolecular Compounds (AREA)
Veneer Processing And Manufacture Of Plywood (AREA)
Processes Of Treating Macromolecular Substances (AREA)
Processing Of Solid Wastes (AREA)
Treatment Of Liquids With Adsorbents In General (AREA)
Solid-Sorbent Or Filter-Aiding Compositions (AREA)

US15/511,195 2014-09-26 2015-09-25 Adhesive compositions comprising type-II cellulose Active 2036-11-22 US10793646B2 (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
US15/511,195 US10793646B2 (en)	2014-09-26	2015-09-25	Adhesive compositions comprising type-II cellulose

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US201462056072P	2014-09-26	2014-09-26
PCT/US2015/052438 WO2016049569A1 (en)	2014-09-26	2015-09-25	Adhesive compositions comprising type-ii cellulose
US15/511,195 US10793646B2 (en)	2014-09-26	2015-09-25	Adhesive compositions comprising type-II cellulose

Publications (2)

Publication Number	Publication Date
US20170275384A1 US20170275384A1 (en)	2017-09-28
US10793646B2 true US10793646B2 (en)	2020-10-06

Family

ID=55582116

Family Applications (4)

Application Number	Title	Priority Date	Filing Date
US15/511,183 Active 2035-11-27 US10385140B2 (en)	2014-09-26	2015-09-25	Cellulose-containing compositions and methods of making same
US15/511,195 Active 2036-11-22 US10793646B2 (en)	2014-09-26	2015-09-25	Adhesive compositions comprising type-II cellulose
US16/541,019 Active 2036-10-08 US11440974B2 (en)	2014-09-26	2019-08-14	Cellulose-containing compositions and methods of making same
US17/880,551 Active US11649296B2 (en)	2014-09-26	2022-08-03	Cellulose-containing compositions and methods of making same

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
US15/511,183 Active 2035-11-27 US10385140B2 (en)	2014-09-26	2015-09-25	Cellulose-containing compositions and methods of making same

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
US16/541,019 Active 2036-10-08 US11440974B2 (en)	2014-09-26	2019-08-14	Cellulose-containing compositions and methods of making same
US17/880,551 Active US11649296B2 (en)	2014-09-26	2022-08-03	Cellulose-containing compositions and methods of making same

Country Status (12)

Country	Link
US (4)	US10385140B2 (zh)
EP (4)	EP3186286B1 (zh)
KR (1)	KR20170066408A (zh)
CN (2)	CN106817901A (zh)
AU (5)	AU2015320328B2 (zh)
BR (2)	BR112017006012A2 (zh)
CA (2)	CA2962606C (zh)
FI (2)	FI3186326T3 (zh)
PL (1)	PL3186286T3 (zh)
SG (3)	SG10202003336XA (zh)
WO (2)	WO2016049567A1 (zh)
ZA (2)	ZA201702794B (zh)

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CA2962604C (en)	2014-09-26	2018-10-02	Renmatix, Inc.	Methods for preparing and collecting polyaromatic compounds, and products comprising polyaromatic compounds
SG10202003336XA (en)	2014-09-26	2020-05-28	Renmatix Inc	Cellulose-containing compositions and methods of making same
WO2017171317A1 (ko) *	2016-03-29	2017-10-05	한국화학연구원	비 산처리 친환경 셀룰로오스 나노결정체의 제조방법 및 이로 제조된 셀룰로오스 나노결정체
US20180016355A1 (en) *	2016-07-14	2018-01-18	Api Intellectual Property Holdings, Llc	Solvent-based processes for producing nanocellulose, and compositions and products produced therefrom
CN108264569B (zh) *	2017-01-03	2020-01-03	中国科学院金属研究所	一种纤维素ii型纳米晶粒子及其制备方法和应用
BR112020000048A2 (pt) *	2017-07-05	2020-07-14	Renmatix, Inc.	fabricação, isolamento, purificação e usos de partículas de celulose de tamanho de partícula pequeno e composições
EP3677241B1 (en)	2017-08-28	2023-02-15	Kuraray Noritake Dental Inc.	Non-solvent-type adhesive composition for dental use
AU2019206607B2 (en) *	2018-01-12	2024-05-23	Circ, Inc.	Methods for recycling cotton and polyester fibers from waste textiles
FI129209B (en) *	2018-02-07	2021-09-15	Andritz Oy	Process for producing microcrystalline cellulose
SE1850470A1 (en)	2018-04-20	2019-10-21	Stora Enso Oyj	Adhesive formulation comprising lignin
KR102073898B1 (ko) *	2018-05-28	2020-02-05	씨제이제일제당 주식회사	멤브레인 여과가 가능한 물리적 전처리된 바이오매스 조성물
KR102134409B1 (ko) *	2018-05-28	2020-07-16	씨제이제일제당 주식회사	고농도의 바이오매스를 포함하는 물리적 전처리된 바이오매스 조성물
WO2019230970A1 (ja) *	2018-06-01	2019-12-05	旭化成株式会社	化学修飾されたセルロース微細繊維を含む高耐熱性樹脂複合体
JP7149885B2 (ja) *	2019-03-22	2022-10-07	株式会社ダイセル	セルロース誘導体粒子、化粧品組成物及びセルロース誘導体粒子の製造方法
WO2024049833A2 (en) *	2022-08-30	2024-03-07	Isp Investments Llc	Water-soluble, partially biodegradable dihydroxyalkyl cellulose

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